DD254733A5 - Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen - Google Patents

Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen Download PDF

Info

Publication number: DD254733A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; integer; iii; compounds; reaction
Prior art date: 1986-03-04

Application number

DD87300370A

Other languages

German (de)

English (en)

Inventor

Guenter Schulz

Walter Trautmann

Hubert Sauter

Wolfgang Mackenroth

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-03-04

Filing date

1987-03-02

Publication date

1988-03-09

1987-03-02 Application filed by ��@��k�� filed Critical ��@��k��

1988-03-09 Publication of DD254733A5 publication Critical patent/DD254733A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title description 3
150000001336 alkenes Chemical class 0.000 claims abstract description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004429 atom Chemical group 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
239000000460 chlorine Chemical group 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
239000011737 fluorine Chemical group 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims description 12
238000000034 method Methods 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 abstract description 16
150000003852 triazoles Chemical class 0.000 abstract description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 5
-1 triazole compounds Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
239000012991 xanthate Substances 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical class CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
PDXFUJVIOGGQKV-UHFFFAOYSA-N 8-(2-fluorophenoxy)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)octan-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)CCCCOC1=CC=CC=C1F PDXFUJVIOGGQKV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000004967 organic peroxy acids Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
WKUFCSWRFAEHSS-UHFFFAOYSA-N 1-(5-bromopentoxy)-2-fluorobenzene Chemical compound FC1=CC=CC=C1OCCCCCBr WKUFCSWRFAEHSS-UHFFFAOYSA-N 0.000 description 1
JACZGSAOIAGXMM-WQLSENKSSA-N 1-[(z)-7,7-dimethyloct-5-enoxy]-2-fluorobenzene Chemical compound CC(C)(C)\C=C/CCCCOC1=CC=CC=C1F JACZGSAOIAGXMM-WQLSENKSSA-N 0.000 description 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
SZOKBCWEWMVWRZ-UHFFFAOYSA-M 5-(3-fluorophenoxy)pentyl-triphenylphosphanium bromide Chemical compound [Br-].FC1=CC=CC(OCCCCC[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SZOKBCWEWMVWRZ-UHFFFAOYSA-M 0.000 description 1
OXPIKSVFUNCAFX-UHFFFAOYSA-N 8-(2-fluorophenoxy)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)octan-1-ol Chemical compound C1=NC=NN1C(CC(C)(CO)C)CCCCOC1=CC=CC=C1F OXPIKSVFUNCAFX-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000005293 duran Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000007306 turnover Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD87300370A 1986-03-04 1987-03-02 Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen DD254733A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863606947 DE3606947A1 (de)	1986-03-04	1986-03-04	Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen und zwischenprodukte hierfuer

Publications (1)

Publication Number	Publication Date
DD254733A5 true DD254733A5 (de)	1988-03-09

Family

ID=6295407

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87300370A DD254733A5 (de)	1986-03-04	1987-03-02	Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen

Country Status (14)

Country	Link
EP (1)	EP0236884B1 (cs)
JP (1)	JPS62212376A (cs)
AT (1)	ATE59384T1 (cs)
CA (1)	CA1305156C (cs)
CS (1)	CS268171B2 (cs)
DD (1)	DD254733A5 (cs)
DE (2)	DE3606947A1 (cs)
DK (1)	DK108387A (cs)
ES (1)	ES2019313B3 (cs)
GR (1)	GR3001514T3 (cs)
HU (1)	HU199434B (cs)
IL (1)	IL81677A (cs)
PL (1)	PL149238B2 (cs)
ZA (1)	ZA871509B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3642632A1 (de) *	1986-12-13	1988-06-23	Basf Ag	Verfahren zur herstellung von phenoxysubstituierten estern und zwischenprodukte hierfuer
US20110160056A1 (en) *	2008-09-09	2011-06-30	Basf Se	Triazole compounds, the use thereof and preparations containing these compounds
EP2334654A1 (de) *	2008-09-09	2011-06-22	Basf Se	Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel
WO2010029065A1 (de) *	2008-09-10	2010-03-18	Basf Se	Imidazol- und triazolverbindungen, ihre verwendung sowie sie enthaltende mittel
CN102149707A (zh) *	2008-09-10	2011-08-10	巴斯夫欧洲公司	咪唑和三唑化合物、其应用和含有所述化合物的试剂
WO2010029066A1 (de) *	2008-09-10	2010-03-18	Basf Se	Imidazol- und triazolverbindungen, ihre verwendung sowie sie enthaltende mittel

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK159205C (da) *	1983-03-16	1991-03-04	Pfizer	Bis(triazol)alkanol-forbindelser, anvendelse af disse, farmaceutiske praeparater og landbrugsfungicider indeholdende disse og fremgangsmaade til behandling af planter eller froe, som har en svampeinfektion
DE3321023A1 (de) *	1983-06-10	1984-12-13	Basf Ag, 6700 Ludwigshafen	Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3416444A1 (de) *	1984-05-04	1985-11-07	Basf Ag, 6700 Ludwigshafen	Verfahren zur diastereoselektiven reduktion von (alpha)-triazolylketonen zu ss-triazolylcarbinolen
DE3420227A1 (de) *	1984-05-30	1985-12-05	Basf Ag, 6700 Ludwigshafen	Vinylazole, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von pilzen

1986
- 1986-03-04 DE DE19863606947 patent/DE3606947A1/de not_active Withdrawn
1987
- 1987-02-25 IL IL81677A patent/IL81677A/xx unknown
- 1987-02-28 ES ES87102872T patent/ES2019313B3/es not_active Expired - Lifetime
- 1987-02-28 EP EP87102872A patent/EP0236884B1/de not_active Expired - Lifetime
- 1987-02-28 DE DE8787102872T patent/DE3766986D1/de not_active Expired - Lifetime
- 1987-02-28 AT AT87102872T patent/ATE59384T1/de active
- 1987-03-02 DD DD87300370A patent/DD254733A5/de not_active IP Right Cessation
- 1987-03-02 JP JP62045410A patent/JPS62212376A/ja active Pending
- 1987-03-02 PL PL1987264391A patent/PL149238B2/pl unknown
- 1987-03-03 ZA ZA871509A patent/ZA871509B/xx unknown
- 1987-03-03 HU HU87866A patent/HU199434B/hu not_active IP Right Cessation
- 1987-03-03 CS CS871412A patent/CS268171B2/cs unknown
- 1987-03-03 CA CA000531048A patent/CA1305156C/en not_active Expired - Lifetime
- 1987-03-03 DK DK108387A patent/DK108387A/da not_active Application Discontinuation
1991
- 1991-02-27 GR GR91400236T patent/GR3001514T3/el unknown

Also Published As

Publication number	Publication date
DK108387D0 (da)	1987-03-03
ZA871509B (en)	1988-11-30
CA1305156C (en)	1992-07-14
PL149238B2 (en)	1990-01-31
IL81677A (en)	1992-02-16
DE3766986D1 (de)	1991-02-07
HUT44021A (en)	1988-01-28
DK108387A (da)	1987-09-05
CS141287A2 (en)	1989-05-12
CS268171B2 (en)	1990-03-14
PL264391A2 (en)	1988-04-14
GR3001514T3 (en)	1992-11-23
JPS62212376A (ja)	1987-09-18
EP0236884A1 (de)	1987-09-16
ES2019313B3 (es)	1991-06-16
IL81677A0 (en)	1987-09-16
DE3606947A1 (de)	1987-09-10
EP0236884B1 (de)	1990-12-27
ATE59384T1 (de)	1991-01-15
HU199434B (en)	1990-02-28

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

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